Potassium Carbonate → N-benzyl-N-methyl-3-azabicyclo[3.2.1]octan-8-amine

HRID 411548Notes

Reaction equation

HRID 411548 reaction equation
[CH2:1]([N:8]([CH3:23])[CH:9]1[CH:14]2[CH2:15][CH2:16][CH:10]1[CH2:11][N:12](C(=O)C(F)(F)F)[CH2:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+]>CO.O>[CH2:1]([N:8]([CH3:23])[CH:9]1[CH:14]2[CH2:15][CH2:16][CH:10]1[CH2:11][NH:12][CH2:13]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 185409031-{8-[Benzyl(methyl)amino]-3-azabicyclo[3.2.1]oct-3-yl]-2,2,2-trifluoro-1-ethanone

Product 1

HCID 18540962N-benzyl-N-methyl-3-azabicyclo[3.2.1]octan-8-amineYield 81.4%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A mixture of 1-{8-[benzyl(methyl)amino]-3-azabicyclo[3.2.1]oct-3-yl}-2,2,2-trifluoro-1-ethanone (see step (vi) above; 2.1 g, 6.4 mmol) and K2CO3 (3 g, 21.7 mmol) in MeOH/water (110 mL of 10:1) was stirred at rt overnight and then evaporated. DCM and water were added and the layers separated. The water layer was extracted with DCM (3×). The combined organic layers were dried and evaporated to give 1.2 g (81%) of the sub-title compound.

Workup

  1. customevaporated
  2. additionDCM and water were added
  3. customthe layers separated
  4. extractionThe water layer was extracted with DCM (3×)
  5. customThe combined organic layers were dried
  6. customevaporated

Sources & evidence

ORD record
ord-e0232775f1684a9898b32180b11633d1
Source dataset
uspto-grants-2003_05
Patent number
US06559162B2

Reaction notes

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